Formation of Toxic α,β-Unsaturated 4-Hydroxy-Aldehydes in Thermally Oxidized Fatty Acid Methyl Esters

To investigate the heat induced formation of alpha,beta-unsaturated 4-hydroxy-aldehydes (4-hydroxy-2-trans-hexenal (HHE), 4-hydroxy-2-trans-octenal (HOE), 4-hydroxy-2-trans-nonenal (HNE) and 4-hydroxy-2-trans-decenal (HDE)) fatty acid methyl esters (FAMEs) of stearic, oleic, linoleic and linolenic acids were heated separately at 185 degrees C for 0 to 6 hrs. The formation of 2,4-decadienal, a suspected intermediate in HNE formation, was also measured in these FAMEs. As expected methyl stearate (MS) and methyl oleate (MO) did not produce any of the alpha,beta-unsaturated 4-hydroxy-aldehydes as a consequence of thermally induced lipid peroxidation. The formation of HHE was detected in both methyl linoleate (ML) and methyl linolenate (MLN), with concentration higher in MLN than in ML. The maximum HHE concentration was 3.99 mu g HHE/g ML after 2 h and 50.78 mu g HHE/g MLN after 4 h of heat treatment. HOE was detected in both ML and MLN, and the maximum concentration was 102.50 mu g HOE/g ML after 6 h and 90.56 mu g HOE/g MLN after 2 h of heating. HNE was found only in ML and its highest concentration was 84.82 mu g HNE/g ML after 3 h of heating. HDE was not detected in any of the four heat treated FAMEs. 2,4-Decadienal was not found to be an intermediate in the formation of HNE in thermally induced oxidation of FAMEs.